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The problem with reaching your career goal

Feeling unhappy and unfulfilled can be among the pitfalls of reaching your career goal, experts say

Alan Gertner is the co-founder of the cannabis brand and store Tokyo Smoke, which sells coffee, clothing and marijuana paraphernalia. He is in the Adelaide St. W shop. This is for a series on the problem with reaching your goal.
(Richard Lautens / Toronto Star)

This is part of an occasional series addressing the problems that can arise after meeting a long-sought goal.

Alan Gertner grew up being told to keep his head down, work hard and get promoted. That’s what he did.

By his mid-20s, the Toronto native landed his dream job. He had a high-profile gig at Google, where he worked for six years, raking in a high salary, travelling all over the world and living in New York, San Francisco, Bangkok and Singapore.

At 30, he was overseeing a large sales team for the tech giant. But his climb up the corporate ladder meant there were “endless trade-offs,” sometimes at the expense of personal relationships.

“I definitely didn’t feel the level of satisfaction or fulfilment that I expected to,” recalls Gertner, now 32. “I felt like I had direction forever and then, instantly, I felt lost.”

Feeling lost — or unhappy, or depressed, or anxious — can be among the pitfalls of reaching your career goal, experts say.

Career and workplace psychologist Meghan Reid says many of her clients, including doctors, engineers, lawyers and CFOs, sometimes struggle with feeling stuck.

As in Gertner’s case, she says people often make assumptions about what they think will fulfil them, based on societal or family messages. And when they reach those goals they realize it’s not what they want.

“I’ve worked with a number of people, specifically in their 40s and 50s, who moved up the ladder into management and now they hate it,” the co-owner of Canada Career Counselling says. “They like the details, the hands-on (work) and have described management as babysitting or draining.”

Other reasons for feeling unhappy at the top, she says, is the belief that one isn’t contributing to society in a positive way, feeling burnt-out because there’s no work-life balance or the sensation of having plateaued.

She recommends talking to a career counsellor or career psychologist, noting many workplace benefit plans cover the cost of a psychologist.

“Even if other people think you have a really high-status successful job, that doesn’t lead to your own fulfilment.”

Reid helps clients figure out why their job isn’t a good fit, focusing on their skills, strengths, values, interests and personality. Sometimes, the individual’s personality doesn’t mesh with the job or their values don’t align.

The fix can sometimes be a complete career change, says Reid, whose clients include people who have made drastic transitions, including engineer to pastry chef, school superintendent to financial planner and doctor to stay-at-home mom.

Career expert Barbara Moses, author of What Next?, says achieving lofty goals at a young age — as was the case for Gertner — can leave some people feeling depressed and demotivated.

“For many, they’ve worked so hard to get there, they’ve done it at the expense of family, friendships, personal health,” Moses says. “Some of them start to reflect, ‘Was it really worth it?’ . . . And you can’t even talk to (your friends) because it’s very hard. You’re making this huge amount of money and you’re going to complain to your friends about how unhappy you are?”

The answer may lie in switching careers, or it could be making their job more meaningful or reigniting a passion from earlier years.

Many times, she says, people feel the need to give back in some way.

“That’s probably their greatest desire when they reach a certain age and say, ‘What’s my legacy? Sure, I’ve built this newspaper, or hospital, or steel company, but what’s my legacy?’ A lot of them teach or become involved in not-for-profits.”

Usually, she says, people take a sabbatical from work — they may volunteer or travel — to reflect on next stages in life.

It turns out that Gertner unwittingly followed the advice of both experts.

Around the time that he was beginning to feel lost, Gertner spoke with his mentor at Google about his desire for the next promotion and his determination to achieve it within a specific time frame. The mentor suggested Gertner put his energy and focus into a broader goal.

Gertner applied at Google for a six-week secondment in Ghana, figuring it would give him time to think.

There, he confided in a local tour guide that he was considering quitting Google because he was unhappy.

“He told me something I suspect will always stick with me. He said he either works on something he loves or works to support people he loves. It was an incredible eye-opening moment.”

Soon after, Gertner returned home to Singapore and quit Google. He talked to friends and family about how he was feeling, met with career coaches and pored over books on career development and fulfilment.

“The singular goal I’d had before was to win at work, so the new goal was to win at life. I needed to decide what winning at life meant.”

Being data-oriented, Gertner built a spreadsheet with various metrics, where he would reflect on how happy and meaningful each day was. He also did the things he had long wanted to do, such as becoming a back country ski tour guide in Japan and taking a road trip with friends from London, England, to Mongolia. Over time, his spreadsheet revealed two things: He liked being part of a community and taking on big challenges.

So in March 2015, he returned to Toronto to be closer to friends and family. And, he teamed up with his entrepreneur father Lorne Gertner — who has worked in various industries including the medical marijuana business — to launch the cannabis brand Tokyo Smoke.

There are now two Tokyo Smoke stores in the city — selling coffee, clothing and cannabis paraphernalia — with another location slated to open this month.

“(Tokyo Smoke) is close and meaningful to me in a way that working at a big company wasn’t,” Gertner says. “I’m on a path that’s more true to making my life feel meaningful and who I want to be. But I also need to continue to focus on developing my entire life.”

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